CA2520242A1 - Production de 5-methyl-1-hydrocarbyl-2-pyrrolidone par amination reductrice d'acide levulinique - Google Patents

Production de 5-methyl-1-hydrocarbyl-2-pyrrolidone par amination reductrice d'acide levulinique Download PDF

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Publication number
CA2520242A1
CA2520242A1 CA002520242A CA2520242A CA2520242A1 CA 2520242 A1 CA2520242 A1 CA 2520242A1 CA 002520242 A CA002520242 A CA 002520242A CA 2520242 A CA2520242 A CA 2520242A CA 2520242 A1 CA2520242 A1 CA 2520242A1
Authority
CA
Canada
Prior art keywords
unsubstituted
catalyst
substituted
methyl
pyrrolidone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002520242A
Other languages
English (en)
Inventor
Leo Ernest Manzer
Frank E. Herkes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2520242A1 publication Critical patent/CA2520242A1/fr
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
CA002520242A 2003-03-24 2004-03-23 Production de 5-methyl-1-hydrocarbyl-2-pyrrolidone par amination reductrice d'acide levulinique Abandoned CA2520242A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/396,046 2003-03-24
US10/396,046 US6900337B2 (en) 2003-03-24 2003-03-24 Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid
PCT/US2004/009004 WO2004085349A2 (fr) 2003-03-24 2004-03-23 Production de 5-methyl-1-hydrocarbyl-2-pyrrolidone par amination reductrice d'acide levulinique

Publications (1)

Publication Number Publication Date
CA2520242A1 true CA2520242A1 (fr) 2004-10-07

Family

ID=32988704

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002520242A Abandoned CA2520242A1 (fr) 2003-03-24 2004-03-23 Production de 5-methyl-1-hydrocarbyl-2-pyrrolidone par amination reductrice d'acide levulinique

Country Status (7)

Country Link
US (1) US6900337B2 (fr)
EP (1) EP1613573A4 (fr)
KR (1) KR20060008302A (fr)
AU (1) AU2004223847A1 (fr)
BR (1) BRPI0409015A (fr)
CA (1) CA2520242A1 (fr)
WO (1) WO2004085349A2 (fr)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7244852B2 (en) * 2003-02-27 2007-07-17 Abbott Laboratories Process for preparing 2-methylpyrrolidine and specific enantiomers thereof
US6900337B2 (en) * 2003-03-24 2005-05-31 E. I. Du Pont De Nemours And Company Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid
US7465813B2 (en) * 2005-04-27 2008-12-16 E. I. Du Pont De Nemours + Company Process for making 5-methyl-N-alkyl-2-pyrrolidone from alkyl amine(s) and levulinic acid
US9028874B2 (en) * 2008-01-03 2015-05-12 Cedars-Sinai Medical Center Antioxidant nanosphere comprising [1,2]-dithiolane moieties
US8603531B2 (en) * 2008-06-02 2013-12-10 Cedars-Sinai Medical Center Nanometer-sized prodrugs of NSAIDs
JP5564512B2 (ja) 2008-11-24 2014-07-30 セダーズ−シナイ メディカル センター 抗酸化カンプトセシン誘導体及びその抗酸化、抗新生物ナノスフェア
US8350056B2 (en) * 2008-12-04 2013-01-08 E I Du Pont De Nemours And Company Functionalized N-substituted pyrrolidonium ionic liquids
JP2012511018A (ja) * 2008-12-04 2012-05-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 伸長リンカーを有するｎ−置換ピロリドニウムイオン液体
US8119818B2 (en) * 2008-12-04 2012-02-21 E. I. Du Pont De Nemours And Company Functionalized N-substituted pyrrolidonium ionic liquids
CN102307647A (zh) 2008-12-04 2012-01-04 纳幕尔杜邦公司 二氧化碳移除和可用于其中的离子液体化合物
US8138354B2 (en) 2008-12-04 2012-03-20 E. I. Du Pont De Nemours And Company N-substituted pyrrolidonium ionic liquids
EP2611764A4 (fr) 2010-08-30 2016-12-14 Arzeda Corp Route de fermentation pour la production d'acide lévulinique, d'esters de lévulinate, de valérolactone, et de certains de leurs dérivés
CN103274982B (zh) * 2013-06-24 2015-10-28 陕西师范大学 乙酰丙酸转化生成内酰胺的方法
CN108129372A (zh) * 2016-12-01 2018-06-08 中国科学院大连化学物理研究所 一种制备环内酰胺衍生物的方法
BR112021006553A2 (pt) 2018-12-04 2021-07-13 Virox Technologies Inc. composições antimicrobianas contendo c3-c5 n-alquil-gama-butirolactama e usos dos mesmos
CN110615754A (zh) * 2019-09-16 2019-12-27 浙江工业大学 一种5-甲基-2-吡咯烷酮的合成方法
KR102540021B1 (ko) 2020-12-02 2023-06-07 (주)유케이케미팜 대량 생산에 적합한 미르타자핀의 제조방법
CN114950449B (zh) * 2022-03-03 2023-07-11 中国科学技术大学 一种多相催化剂及其制备方法和应用
CN114934082B (zh) * 2022-04-29 2024-03-26 华东理工大学 一种连续流生物催化合成(s)-5-甲基-2-吡咯烷酮的方法
CN116550362A (zh) * 2023-04-28 2023-08-08 浙江工业大学 一种FeNi@NC双金属催化剂及其制备方法和应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681349A (en) * 1952-03-11 1954-06-15 Quaker Oats Co Preparation of 5-methyl-2-pyrrolidone
US3235562A (en) * 1962-01-29 1966-02-15 Crown Zellerbach Corp Making lactams by the vapor phase reductive amination of oxo carboxylic acid compounds
GB1036694A (en) 1964-03-03 1966-07-20 Wyeth John & Brother Ltd Substituted aminocarboxylic acid derivatives and compositions containing such derivatives
US4590190A (en) * 1983-07-01 1986-05-20 Nitto Electric Industrial Co., Ltd. Method for percutaneously administering physiologically active agents using an alcohol adjuvant and a solvent
US5156666A (en) * 1989-12-11 1992-10-20 Isp Investments Inc. Delivery system for agricultural chemicals
US5302197A (en) * 1992-12-30 1994-04-12 E. I. Du Pont De Nemours And Company Ink jet inks
US5922660A (en) * 1995-12-07 1999-07-13 Colgate-Palmolive Co. Composition
US6962665B2 (en) * 2000-12-08 2005-11-08 E. I. Du Pont De Nemours And Company Refrigerant compositions containing a compatibilizer
US6743819B1 (en) * 2003-03-24 2004-06-01 E. I. Du Ponte De Nemours And Company Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid with aryl amines
US6900337B2 (en) * 2003-03-24 2005-05-31 E. I. Du Pont De Nemours And Company Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid

Also Published As

Publication number Publication date
EP1613573A4 (fr) 2008-10-29
WO2004085349A2 (fr) 2004-10-07
EP1613573A2 (fr) 2006-01-11
BRPI0409015A (pt) 2006-03-28
WO2004085349A3 (fr) 2006-05-04
KR20060008302A (ko) 2006-01-26
US20040192933A1 (en) 2004-09-30
AU2004223847A1 (en) 2004-10-07
US6900337B2 (en) 2005-05-31

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US6900337B2 (en) Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid
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US7129362B2 (en) Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive of levulinic acid esters with aryl and alkyl amines
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CA2520448A1 (fr) Production de n-(methyl-aryl)-2-lactame, n-(methyl cycloaklyl)-2-lactame et n-alkyl-2-lactame par amination reductrice de lactones avec des composes aryle et alkylcyano
CA2520431A1 (fr) Production de 5-methyl-n-(methylaryl)-2-pyrrolidone, de 5-methyl-n-(methylcycloalkyl)-2-pyrrolidone et de 5-methyl-n-alkyl-2-pyrrolidone
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CA2520860A1 (fr) Production de n-aryl-2-lactame et de n-alkyl-2-lactame par amination reductrice de lactones avec des composes nitro aryliques et alkyliques

Legal Events

Date Code Title Description
FZDE Discontinued